N-(5-amino-4-fluoro-2-methylphenyl)acetamide → N-[5-[[3-cyano-7-(cyclobutylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-4-fluoro-2-methylphenyl]acetamide

HRID 722

반응식

HRID 722 반응식
CC(=O)Nc1cc(N)c(F)cc1C.N#Cc1cnn2c(NC3CCC3)cc(Cl)nc12>CC(=O)N(C)C.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CC(=O)Nc1cc(Nc2cc(NC3CCC3)n3ncc(C#N)c3n2)c(F)cc1C

참가 물질

7

반응물 2

HCID 89099132N-(5-amino-4-fluoro-2-methylphenyl)acetamideHCID 178418221HCID 178418221, 화합물

생성물 1

HCID 72164043N-[5-[[3-cyano-7-(cyclobutylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-4-fluoro-2-methylphenyl]acetamide수율 5.51%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

5-chloro-7-(cyclobutylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (80 mg, 0.32 mmol), N-(5-amino-4-fluoro-2-methylphenyl)acetamide (58.8 mg, 0.32 mmol), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (18.69 mg, 0.03 mmol) in DMA (5 mL) were added to a microwave tube. Pd2(dba)3 (14.79 mg, 0.02 mmol) and cesium carbonate (210 mg, 0.65 mmol) were added. The solution was degassed, filled with N2, capped, then microwaved at 150C for 30 min. The organic solvent was removed. TLC showed two closely associated peaks, so product was purified via Gilson. Appropriate fractions were collected, concentrated by rotovap, and dried in the oven overnight. LCMS, HPLC, and NMR revealed desired product. See attachments.

출처 및 근거

ORD 기록
ord-b55c5711f803482494d33a05fbba3389
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
출처 보기

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